Enhanced diastereoselectivity via confinement: Photoisomerization of 2,3-diphenylcyclopropane-1-carboxylic acid derivatives within zeolites

J. Sivaguru, Raghavan B. Sunoj, Takehiko Wada, Yumi Origane, Yoshihisa Inoue, Vaidhyanathan Ramamurthy

Research output: Contribution to journalArticlepeer-review

32 Scopus citations

Abstract

From the perspective of asymmetric induction, the photochemistry of 24 chiral esters and amides of cis-2,3-diphenylcyclopropane-1-carboxylic acid from excited singlet and triplet states has been investigated within zeolites. The chiral auxiliaries placed at a remote location from the isomerization site functioned far better within a zeolite than in solution. Generally, chiral auxiliaries with an aromatic or a carbonyl substituent performed better than the ones containing only alkyl substituents. A model based on cation-binding- dependent flexibility of the chiral auxiliary accounts for the observed variation in de between aryl (and carbonyl) and alkyl chiral auxiliaries within zeolites. Cation-dependent diastereomer switch was also observed in select examples.

Original languageEnglish (US)
Pages (from-to)6533-6547
Number of pages15
JournalJournal of Organic Chemistry
Volume69
Issue number20
DOIs
StatePublished - Oct 1 2004
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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